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There’s Risk With ‘Win Now Mode’

This is going to be a very interesting offseason for the Edmonton Oilers. They have some clear holes that need to be filled and not a lot of cap space to work with. Their problems are not unique though. It feels like 90% of the NHL is looking to shed either cap space or straight-up salary while still improving their roster. That will make it even more difficult for Ken Holland to do what he needs to do over the next few months.

I read a lot of comments from fans and it seems like a large portion of the fan base is clamouring for the Oilers to make significant moves to make themselves a legitimate Stanley Cup Contender. ‘Win Now Mode’ is the phrase that gets thrown around and honestly, I’m not sure if I’m a fan of that term anymore.

It feels like whenever someone says that the Oilers need to be in win-now mode, they immediately bring up trading the 14th overall pick or other significant future assets. To me, the Oilers mindset should not be that they need to trade first-round picks to be in ‘win-now mode’. I don’t agree with that line of thinking.

I understand why some fans say that the Oilers need to be doing everything they can to become legitimate Stanley Cup contenders as quickly as possible but at the same time, there needs to be just as much emphasis on them building a sustainable contender. Connor McDavid is under contract for six more years and Leon Draisaitl is here for five more. I want to see Ken Holland build a team that is a perennial threat to go deep in the playoffs and to do that, you sometimes need to make decisions with the future in mind.

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The people who say that Connor McDavid will be frustrated and will request a trade if the Oilers miss the playoffs again are trolls. I don’t think that the Oilers Captain will request a trade anytime soon. Holland was not brought here to do whatever it takes to win a Stanley Cup in his first two seasons on the job, he was brought here to build a strong organization that can consistently be in a position to win a championship.

What I’m really trying to say is that “going all in” should not be the mindset. You need to keep one eye on the future and one eye on next season.

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I’m not completely against Holland trading first-round picks or anything like that, but it needs to be an absolute slam dunk deal if he’s going to do it. Looking at the long-term future of the Oilers, they’re going to have a lot of money tied up in Draisaitl, McDavid, and Ryan Nugent-Hopkins and they’ll need to compliment them with good players on cheap contracts. The best way to do that is to draft well and have players produce while they’re still on their ELC’s. That’s why I’d be very hesitant to trade the 14th overall pick.

Don’t take this as me saying that Ken Holland should sit on his hands and have an offseason that would make Steve Tambellini smile. He needs to go out and fill some holes in this lineup. The Oilers need a third-line centre that can produce offence and a reliable goaltender to play with Mikko Koskinen. If Holland doesn’t acquire those then this offseason will be a failure. But he can get those players without giving up significant future assets. There will be a chance to make smart deals in an offseason where many teams are feeling financial pressure. 

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I’ve seen people throw out the idea that the Oilers need to do their best to acquire Oliver Ekman-Larsson or need to find the cap space to sign a top-six scoring winger like Taylor Hall or Mike Hoffman. That just doesn’t make sense to me. Even if they could find a way to afford one of those players for next season, it’s just going to create an even bigger cap crunch down the road.

The reality of the current situation facing NHL GM’s is that the cap is going to be staying flat for the next few seasons and there won’t be any compliance buyouts to magically help clear up cap space. Now, more than ever, it’s important to pinch your pennies and make sure you don’t wind up in cap hell. I don’t want to see the Oilers buy out a player like James Neal, just to make a slight upgrade to their forward core. I believe they can build a strong forward group without adding more dead cap space to their books.

I think it’s a poor idea to try to move out a bunch of cap space and assets just to spend it on an expensive free agent. The Oilers need better depth and they won’t solve that problem by trading a package of assets for Ekman-Larsson or for the cap space necessary to get a guy like Alex Pietrangelo and even if they did, it might result in them losing a quality player in the expansion draft.

With Connor McDavid and Leon Draisaitl, the Oilers have a great chance to not win just one Stanley Cup, but multiple. That should be the goal. To do that, you can’t look at one season and decide to spend all your assets to take one big swing at the Stanley Cup.